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Episode 13

Episode 13: Hire Lucky Generals: Building a Winning Team through Talent Acquisition


Winning isn’t about luck; it’s the result of careful planning and preparation. Just as a military unit relies heavily on its leaders for effective planning, cohesion, and teamwork, businesses must make sure to assemble a team with leadership potential. In this episode of Veteran Led, John Berry will discuss the importance of recruiting the right individuals who bring valuable experience, leadership skills, and the ability to navigate challenges, ultimately driving team members, and the organization forward.


Welcome fellow veterans. From the tip of the spear to in the rear with the gear, I went from active-duty Infantry to reserve-component logistician. I’m your host, CEO, entrepreneur, trial lawyer, and Lieutenant Colonel Retired, John Berry. The military lessons that I learned helped me grow an eight-figure business that has maintained consistent annual double-digit growth, landing on the Inc. 5000 list of fastest growing companies in America every year for the past seven years, and has allowed me to continue to serve America’s heroes.

Welcome to Episode 13: Hire Lucky Generals.

Hire lucky generals. When critics attacked Napoleon Bonaparte for his battlefield wins, saying that they had nothing to do with skill or strategy, but were a matter of luck, Napoleon famously retorted, “I’d rather have lucky generals.” Over a century later, General Eisenhower said, “I’d rather have lucky generals. They win battles.”

For most of us, we understand that winning has little to do with luck, and the lucky generals will credit their team, the plan, or the conditions on the battlefield for the win, but they will never say, “I got lucky.” Similarly, unlucky people tend to blame luck rather than their own decisions, their bad life choices, or their poor relationships. The lucky take accountability. And I want to talk a little bit about who that lucky general may be in your organization. Let me ask you a question. Who is your best team member? The answer is you haven’t hired that team member yet. Your best hires will come in the future. You want to hire lucky generals, people who have actually won the battles, people who have been there and done that.

As you grow your organization, you will need to hire even better leaders. And you need to hire the leaders that have won the battles that you need to fight to get to the next level. And yes, the lucky generals have done it, and the untested leaders who claim they know how to do it, but haven’t done it, are a risk. The lucky generals are a much better bet.

We all know the lucky soldier in the military. They were soldier of the quarter, they seemed to never draw CQ duty on the weekend, everything seemed to go their way. It was kind of like they might as well just be buying a lottery ticket every now and then because they were just so lucky. But we also know the unlucky team member too; the universe conspires against them, their past results tell the story, and they just can’t catch a break. Everything is everybody else’s fault.

I remember a story about an ROTC cadet. This ROTC cadet used to work at Berry Law, and he told us a story about he was on his way to training, and he legitimately got a flat tire, and so he was 30 minutes late. The noncommissioned officer running the training said, “Oh, cadet, I see how this is. You failed to allocate enough travel time to account for contingencies. So, you failed to plan. This flat tire has nothing to do with luck. It has to do with your failure to understand that as a leader, you must plan for contingencies.”

Lucky generals get that. They get lucky because if something bad happens, they already have a contingency plan. These types of leaders are indispensable on your team because guess what? In business, things go bad, and you need someone who can plan, create a contingency plan and someone who doesn’t get rattled because they know what it takes because they’ve been there and they’ve won the battle, luck or not.

Past results matter and the lucky generals get those results. So where do you find lucky generals? Well, you have to start with one. You already know one. You know someone who has gotten to the level that you want to be at, and that’s where you start. Start with the lucky generals and find out, who are the other lucky generals they know. Greatness follows greatness.

When I recruit for a lucky general, I’m recruiting three to four people at a time, and I think that if I can hire all three lucky generals, I’ll do it. There is always room at the top. Even if I don’t have a space for them, I will create one because that is an investment that I can make all day long because it helps scale the organization and it will pay for itself. Lucky generals hang out with other lucky generals, and they’re going to tell them about my organization, and that’s going to open up more opportunities. They know that I’m building an army, and the best generals want to lead good armies. And if they see the opportunity, they’re going to come to your team.

Now, that being said, think of the opposite of the lucky general; think back to the military. When I was an officer, trying to get to 20 years as an officer, if you didn’t make the rank of lieutenant colonel, you couldn’t get your 20 in. You could only serve, I can’t remember, it was 8 to 10 years as a captain, before they’d boot you out for not getting promoted. It was move up or move out. And the lucky generals are the individuals in the organization that understand that the organization is moving upward, and they want to grow and develop themselves, but also the team members.

My brother, who was a naval officer, used to work for our company said, we could only hire on the upswing. And what he meant by that was we wanted people on the team who wanted to build the bigger future with us, who wanted more out of life. We didn’t want to hire someone who was interested in coming to our team just to retire or just to hang out or just to mail it in; we wanted a difference-maker. We wanted someone who would come in and win our battles. And so, if they’re not on the upswing, we generally are not going to be a good fit.

And I know that’s different than corporate America, where someone can work at the same job for 20+ years, showing minimal improvement, but they’re a cog in a big corporate machine, and so it works. In a smaller, more entrepreneurial company, or a company that’s focused on growth, that position, those people don’t keep up. And it’s just the sad reality because your top talent today will not be your top talent tomorrow. And if members of the team don’t want to get on the upswing, they’re not going to make it.

And your lucky generals want to get everybody on board to grow, to go to the next level. Because once again, they’ve been there. And I can’t emphasize how important they are because they’ve been to the level that your company has not yet been to. And so, when you can hire someone who’s been to the promised land, it makes all the difference. They know things that you don’t know, and they can foresee problems that you can’t yet see because you haven’t been there.

Now, no person stays with the team forever. And I know a lot of officers who say, “Look, I would be a platoon leader my entire career if I could. It was such a great experience.” But that can’t be the mentality in your organization. You need racehorses. And the racehorses, if you want to hire them, they’re going to come to the stable and sniff around and say, “Do you have other racehorses on your team?” You don’t want to hire a racehorse, that lucky general who wants to win, and they come to a stable full of donkeys. Because you can’t take a donkey to the racetrack. I learned that from a friend, Alexander Shunnarah, in Alabama. You can’t take a donkey to the racetrack.

The winners, the lucky generals, are like thoroughbreds. They’re here to win the race and they want to be around other thoroughbreds. They want to run fast and they want to win and they’re excited. And when they come to your team, you can just feel the energy because they want to build something great, and they want to win.

Now, if you have team members that are not excited about growth, about the next level, improvement, and challenges, you’ve built the wrong team. See, the company leadership must be the steward of the company. And that means taking the company to the next level and ensuring that all the individuals in your charge, just like the military, you deploy overseas, you’re not only responsible for completing the mission, but for protecting America’s sons and daughters. When you run a company, you’re responsible for the financial security of your team members; make sure they have jobs, make sure the company isn’t going to go under because most of your team members are really concerned with safety, and safety is an illusion.

Think about your kids. Your kids, you want to protect them, you want to make sure that they’re safe. You’d probably make them wear protective gear when they leave the house if you could, right? But the reality is you can’t make your kids safe. You can make them strong. You can make them smart. At the end of the day, their strength and their intelligence, that’s what’s going to keep them safe, not all the padding you put on them, not how much you try to coddle and protect them.

Similarly with team members, there’s no safety in any organization. We saw that in 2008, a bunch of big corporations fell apart. We saw that happen in 2020, right? People lost jobs. That always happens in corporate America. Where is the safety? The safety is in developing your own individual skills. And if you’re a great organization, you’re encouraging your team members to grow those skills, to get better. And that’s where the organization can have safety. Safety is in excellence. Safety is not in the mediocre. If you’re excellent, there will always be a demand and you will always be in demand.

Companies are always looking to hire, and the safety comes from being that next level team player, where even if your organization fell apart tomorrow, you’d have done such a great job leading your team members that other organizations would be hungry to snap them up. That way, you’ve provided safety, economic safety, financial safety for your team, because you’ve developed team members with skills that allow them to survive wherever they are.

Now, that being said, who is the next hire on your leadership team? Well, first of all, if you’re the leader, one of the best things you can do is hire for your greatest area of weakness. You want to develop your strengths as a leader. And there’s a lot of things you’re probably not good at. You may be great at the HR piece, but bad at finance. You may be great at sales and marketing, but horrible at operations. That’s fine. You as a leader should work on your strengths, find out where you’re weakest, or the organization’s weakest; that’s your next hire. That’s where you need a lucky general to grow the organization and make it stronger and more resilient.

Number two, look at your biggest pain points and your biggest time sucks. Where are you spending time that you don’t need to be spending time? Hire a lucky general to dig you out there. Or what do you dread at work? Lucky general will take that off your plate. If you want to have an immediate impact in your organization, you’re not going to do it by yourself. You need to hire someone who can have that effect. Once again, someone who has been where you’re going.

When you hire that top performer, who has a huge track record of success, the team knows it. It’s like an instant energy injection to the team; everybody feels it. I had this happen where I hired a senior team member from a law firm five times the size of ours, who was well-respected in the community. As soon as we brought him on, the culture changed. Other lawyers wanted to be like him. They wanted to emulate him, and they saw him as greatness. And they saw me as someone who celebrated greatness, and it affected the entire organization. So, when you hire for effect, kind of like field artillery, a fire for effect, right? Once you hire for effect, the organization really feels it. And so, you have to be intentional about how is this person going to help the organization? Similarly, if you’re not really intentional about how you’re hiring for effect, you may hire someone who’s a dud, who will drag down the morale of the team. So, you need to be cognizant of it.

Now, when you hire someone great, especially in a leadership position, you can’t be the one that is making the decisions about who’s qualified to stay, and who needs to move on. And so, you need to hire people who have the strength to fire. I know this is very difficult for a lot of people to hear, but in the military, you learn something that was not helpful, which was that if someone could not perform at the next level, you as a leader fail.

And I had a sergeant major tell me, they said, “Lieutenant!” And this is when I was the support platoon leader. I went from infantry line platoon leader to support platoon leader. And what would happen is, you probably are familiar with the concept, I would get all the rejects that the platoons didn’t want, and they would add them to the support platoon. Which, okay, if you want logistical support, why not give me your best people? But I went to the sergeant major and said, “Look, I’ve got a whole roster full of problems and I’m just, the support platoon is just a dumping ground for problem children.” Sergeant major said, “Look, Lieutenant, these soldiers scored high enough on the ASVAB, they’re physically fit, they’re mentally stable, they cleared all the hurdles to be in the military. If you can’t get them to the next level, that’s a leadership problem.” Okay, and I carried that with me for a long time as a civilian leader, thinking that if I couldn’t bring a team member to the next level, it was a leadership failure on my part. But that’s absolutely not true.

And you need some of those lucky generals who will say, “You know, this person does not have the skills, nor will they develop the skills, and we need someone else to replace them to go to the next level.” And, like I said, lucky generals, they get that. Formerly great performers who become underperformers in the organization create a lot of emotional baggage for leaders. It takes a lot of strength to fire someone, but it takes even more strength to fire someone that you once admired, especially when you recognize that this person may have got you from point A to point B, and now they’re just not capable of getting you to point C. It’s a very tough thing to do as a leader.

But what about no soldier left behind? What about not leaving a fallen comrade? Well, there’s a difference between leaving a fallen comrade on the battlefield and an administrative discharge in the military, right? You may say, we take care of our own and we want to make sure that everybody’s successful, but you get back into garrison and look, people are being chaptered out, unsatisfactory performance, weight loss issues, physical fitness, going AWOL; all these things can lead to a soldier getting separated from the organization.

So how do we as leaders make retention decisions? As I said, we want to get lucky generals, but the lucky generals aren’t going to stay if they feel like we don’t have a great team. Well, it all starts with the recruiting and hiring process. You need to hire on schedule. We have a 36-month schedule. We know when we’re going to hire along those months. If at any point, we see a candidate who is going to fit that position, maybe it’s a quarter too early, maybe it’s a year too early, we’re hiring because the worst thing you can do is wait to hire, be late to hire, and then you’re just looking for a warm body at that point. You need time to make great hires. And hires are always better when time is on your side, when you have the candidates, and you don’t need to hire right now.

The other thing is that you want to hire somebody who has to clear obstacles. I think about in military, they don’t take just anybody. As a recruit, you’ve got to take the ASVAB, have a physical, background checks, and if you don’t pass all that, you don’t get on the team. Similarly, as a leader, when you’re looking at recruiting and retaining, you want to make sure that you’re hiring people who have been through a funnel, who have been properly vetted.

Finally, if you don’t do this, you’re going to pay in progress lost. Seldom things cost more than a bad hire. And when you bring someone on for 90 days to onboard them and you’re paying all those costs and they don’t work out, it’s a real cost and it’s expensive. Number two, if you’re having recruiting and retention issues, you need to look at your onboarding process.

Think about back to when you had a new first sergeant or company commander come into the organization. Yes, that individual could come in and start cleaning things up day one, but that’s because they’d been in the military for what, six, eight, ten years before they came to your unit. And so, the military was nothing new. There was no new culture assimilation. They just had to come to your unit, and they already knew what was wrong and they came in day one and started making changes, but that doesn’t work that way in the civilian world. Someone who is new to your organization is going to take 90 days, maybe six months, to really learn the job and be good at it. So, you have to have a plan to onboard them and make sure they’re trained.

Think about this. You come to a new organization, no one trains you, no one mentors you. The first day you show up, nobody knew you were going to arrive, there’s no desk set up for you, there’s no computer, you’re just standing around waiting, nobody’s talking to you, you’re getting weird looks from everybody. No, you can’t do that in an organization, right? That first impression, you’re thinking, I want out. What did I do? Right? But if you show up the first day, and your desk is there, the computer set up, you already have a sponsor, you’re taken to lunch, you’re treated like the team wants you there, you’re going to stay. And you need to make sure that’s happening in your organization. That first day of the onboarding process through the first 90 days are key to retaining the right people.

Number three, training and development. Training doesn’t stop after the 90-day onboarding. In fact, it keeps going. You should be like a military organization where you have a published training schedule. The training is actually on the calendar, so the team knows that you are serious about training, and you’re serious about giving them a better future.

And finally, we all have perishable skills. Training is imperative. Think about the training you had to do to recertify as a combat lifesaver or going to the range to ensure that you’re qualified. These are things that have to happen regularly for the team to be successful. And so, you can’t say, “Well, they’re onboarded, they’re ready to go.” No, the training may take 90 days, it may take six months, but training is imperative to retaining great people.

Finally, if you’re having retention issues, take a look at the leadership. Good leaders never want to leave great leaders. They always want to be on the team with that leader who is taking them to the next level. Conversely, great leaders will not tolerate poor leaders. In fact, great leaders don’t even tolerate good leaders. One of John Maxwell’s Laws of Leadership; he talks about, “No one will follow a lesser leader.” So, it’s important that the people that you put in charge of others are the great leaders who can develop them. Otherwise, you’re going to lose some of your leaders who have amazing potential, and you don’t want to lose them.

So, are you a lucky general? Are you the type of leader who has won battles that people want to follow? To answer that question, you have to look at who you’ve hired in the past who has personified who you want. I had this woman who worked for us, her name was Lorraine, she worked for the VA for over 30 years, and she wanted to continue to help veterans so, she started working in our practice helping veterans. And she had this gold minivan, and I would show up at work some days at seven in the morning and not leave most days till 7 PM. So, from 0700 to 1900, that gold minivan was there. And I would stop it and talk with her, and she was so happy about the work we were doing with veterans. And she would help train our team members and she was so excited to see them develop, and she couldn’t wait for the next training plan, she couldn’t wait for who she could help next, whether it was a veteran, or one of our team members, she just wanted to help. And that was so infectious to the rest of the team. And while, I can’t say that I made her, she made herself, but getting her on the team was one of my greatest wins as a leader. And that’d be one of yours too. Find your Lorraine. Find that person who shows up early, stays late, motivates the entire team. If you do that and you bring them on your team, you are a great leader.

After Action Review: Number 1. Hire winners. Hire team members who have done the thing that your organization needs to do and have done it successfully. They have been there and done that. Number 2. Hire the person who understands why they won. In that interviewing process, find out why they won. Number 3. Create the environment that attracts lucky generals.

Three Down: Number 1. Unlucky team members make your team unlucky. Number 2. Losing teaches lessons, but it doesn’t teach people how to win. Lucky generals know how to win. Number 3. Unlucky team members never understand why they’re unlucky and you’re not going to be able to fix their broken egos.

Thank you for joining us today on Veteran Led, where we pursue our mission of promoting veteran leadership in business, strengthening the veteran community, and getting veterans all of the benefits that they earned. If you know a leader who should be on the Veteran Led podcast, report to our online community by searching @veteranled on your favorite social channels and posting in the comments. We want to hear how your military challenges prepared you to lead your industry or community, and we will let the world know. And of course, hit subscribe and join me next time on Veteran Led.

Berry Law

The attorneys at Berry Law are dedicated to helping injured Veterans. With extensive experience working with VA disability claims, Berry Law can help you with your disability appeals.

This material is for informational purposes only. It does not create an attorney-client relationship between the Firm and the reader, and does not constitute legal advice. Legal advice must be tailored to the specific circumstances of each case, and the contents of this blog are not a substitute for legal counsel.

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